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Am I allowed to buy 500 shares on July 10th, 2008 (one month after the first sale)

No. They will wash against the June 20 sale. If you bought 1500 shares on that date, 1000 would wash against the June 20 sale, but the June 9 loss would be OK.

Or do I have to wait until July 21st, 2008 to buy all 1500 shares (one month after the final sale)?

Given your sale dates, that's what you'll need to do to avoid wash sale problems.

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